Episode 49: Dreaming BIGGIE Behind the Bar: We Let AI Teach Us Bartending and the Results Were Mixed (Literally)

In Episode 49 of Never Stop Dreaming Biggie, Brian and I are back together for our February Homestead update — and this time, we let AI teach us how to bartend. The results? Mixed. Literally. This episode is equal parts Valentine's chaos, cocktail experiments, marriage conference highlights, and real talk about where we are with The Holmestead Hideaway.We kicked off the weekend at the Seacoast Marriage Conference where we serve on the prayer team and lead the SYMBIS program. We got to meet Les and Leslie Parrott — the creators of SYMBIS — in person after seven years of teaching their material, and walked away with new tools for our marriage (like the three-squeeze hand trick we probably should have used before hitting record). Then we came home, fired up our AI COO Viva, and attempted to make four classic cocktails: a daiquiri, a Negroni, a Manhattan, and the Harry Maude martini. The daiquiri was a disaster. The Negroni was a showstopper. Brian debuted his signature Holmes Fashion old fashioned with homemade Cheerwine simple syrup, and I learned that he's naturally better at stirring than I am — and I'm not happy about it.Whether you're dreaming of opening your own bar, navigating business with your spouse, or just need a good laugh watching two entrepreneurs fumble through cocktail measurements with questionable jiggers and an AI coach, this episode is for you. We also share major updates on The Holmestead Hideaway in Bequia, our search for capital stewards, dreams of bringing Cheerwine and Waffle House to the Caribbean, and plans for our podcast's one-year anniversary at the Charleston Wine and Food Festival.The "G" in BIGGIE stands for Grow — and growing through challenges (not around them) looks a lot like two people standing at a home bar with bad measurements, a shaker that won't open, and a dream that's bigger than any cocktail fail.Key Takeaways:Discover how AI can serve as your bartending coach and business COO (meet Viva)Learn the proper stirring technique that keeps your cocktails quiet and professionalUnderstand why more ice actually means less dilution in your drinksMaster the classic Negroni with gin, sweet vermouth, and CampariCreate Brian's signature Holmes Fashion old fashioned with Cheerwine simple syrupNavigate learning new skills as a couple without losing your mind (or your marriage)Implement the three-squeeze hand trick from Les and Leslie Parrott's marriage teachingsBuild relationships with brands and creators before using their recipes or productsDevelop your bar menu by starting small and perfecting a few signature drinksExplore the capital steward model for funding passion projects and charity-driven businessesPlan phased business launches from friends-and-family testing to pop-ups to full openingConnect with your community through in-home speakeasy-style soft launchesConnect with Us: 🎙 @neverstopdreamingbiggie 📱 @angelpholmes 🌐 sipindipity.com 📧 [email protected] More: 🌴 The Holmestead Hideaway https://theholmesteadhideaway.com/ 👩‍💼 The Brighter Side Society https://sipindipity.com/brighter-side-society 💼 One-on-One Coaching https://sipindipity.com/mentorship-2025 📅 The Brighter Week Waitlist & Free Assessment https://quiz.tryinteract.com/#/6980f62c2606173ca6c95a49